N⁴-acetyl-5'-O-(4,4'-dimethoxytrityl)-5-methyl-2'-O-{[(triisopropylsilyl)oxy]methyl}cytidine

Base Information

• Chemical Name: N⁴-acetyl-5'-O-(4,4'-dimethoxytrityl)-5-methyl-2'-O-{[(triisopropylsilyl)oxy]methyl}cytidine
• CAS No.: 872548-53-3
• Molecular Formula: C₄₃H₅₇N₃O₉Si
• Molecular Weight: 788.026
• Mol file: 872548-53-3.mol

Synonyms:N⁴-acetyl-5'-O-(4,4'-dimethoxytrityl)-5-methyl-2'-O-{[(triisopropylsilyl)oxy]methyl}cytidine

Chemical Property of N⁴-acetyl-5'-O-(4,4'-dimethoxytrityl)-5-methyl-2'-O-{[(triisopropylsilyl)oxy]methyl}cytidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁴-acetyl-5'-O-(4,4'-dimethoxytrityl)-5-methyl-2'-O-{[(triisopropylsilyl)oxy]methyl}cytidine

There total 7 articles about N⁴-acetyl-5'-O-(4,4'-dimethoxytrityl)-5-methyl-2'-O-{[(triisopropylsilyl)oxy]methyl}cytidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

5'-O-(4,4'-dimethoxytrityl)-5-methyl-2'-O-{[(triisopropylsilyl)oxy]methyl}cytidine (872548-51-1) + acetic anhydride (108-24-7) → N4-acetyl-5'-O-(4,4'-dimethoxytrityl)-5-methyl-2'-O-{[(triisopropylsilyl)oxy]methyl}cytidine (872548-53-3)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃; for 8h;

DOI:10.1002/hlca.200590209

Reference yield:

5'-O-(4,4'-dimethoxytrityl)-5-methyl-2'-O-{[(triisopropylsilyl)oxy]methyl}uridine (872548-23-7) → N4-acetyl-5'-O-(4,4'-dimethoxytrityl)-5-methyl-2'-O-{[(triisopropylsilyl)oxy]methyl}cytidine (872548-53-3)

Guidance literature:

Multi-step reaction with 5 steps

1: DMAP / pyridine / 3 h / 20 °C

2: 4-chlorophenyl phosphorodichloridate; iPr₂NEt / acetonitrile / 6 h / 20 °C

3: NH₃ / acetonitrile; dioxane; H₂O / 3 h / 20 °C

4: 0.60 g / NaOH / tetrahydrofuran; methanol; H₂O / 0.5 h / 4 °C

5: 90 percent / dimethylformamide / 8 h / 20 °C

With dmap; sodium hydroxide; ammonia; N-ethyl-N,N-diisopropylamine; 4-chlorophenylphosphorodichloridate; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/hlca.200590209

Reference yield:

Acetic acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-triisopropylsilanyloxymethoxy-tetrahydro-furan-3-yl ester → N4-acetyl-5'-O-(4,4'-dimethoxytrityl)-5-methyl-2'-O-{[(triisopropylsilyl)oxy]methyl}cytidine (872548-53-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 4-chlorophenyl phosphorodichloridate; iPr₂NEt / acetonitrile / 6 h / 20 °C

2: NH₃ / acetonitrile; dioxane; H₂O / 3 h / 20 °C

3: 0.60 g / NaOH / tetrahydrofuran; methanol; H₂O / 0.5 h / 4 °C

4: 90 percent / dimethylformamide / 8 h / 20 °C

With sodium hydroxide; ammonia; N-ethyl-N,N-diisopropylamine; 4-chlorophenylphosphorodichloridate; In tetrahydrofuran; 1,4-dioxane; methanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/hlca.200590209

upstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-5-methyl-2'-O-{[(triisopropylsilyl)oxy]methyl}cytidine

acetic anhydride

5'-O-(4,4'-dimethoxytrityl)-5-methyl-2'-O-{[(triisopropylsilyl)oxy]methyl}uridine

1-((2R,3R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3,4-dihydroxytetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione